1-BENZYL-3-METHYL-4-PIPERIDONE

1-BENZYL-3-METHYL-4-PIPERIDONE Property

Boiling point:

99°C/0.05mmHg(lit.)

Density 

1.0156 (rough estimate)

refractive index 

1.5315-1.5335

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Methanol

pka

7.11±0.40(Predicted)

form 

Liquid

color 

Clear slightly yellow to yellow

InChI

InChI=1S/C13H17NO/c1-11-9-14(8-7-13(11)15)10-12-5-3-2-4-6-12/h2-6,11H,7-10H2,1H3

InChIKey

OVQAJYCAXPHYNV-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(=O)C(C)C1

CAS DataBase Reference

34737-89-8(CAS DataBase Reference)

Safety

Hazard Codes 

C

Risk Statements 

34-22

Safety Statements 

45-36/37/39-26

RIDADR 

2735

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P405Store locked up.

P501Dispose of contents/container to..…

1-BENZYL-3-METHYL-4-PIPERIDONE Chemical Properties,Usage,Production

Chemical Properties

clear slightly yellow to yellow liquid

Uses

1-Benzyl-3-methyl-4-piperidone is a piperidine derivative used in the preparation of Fentanyl (F274990) analogs with analgesic activity.

Synthesis

A solution of 1-benzylpiperidin-4-one (60 g, 0.3 mol) in THF (100 mL) was slowly added dropwise to a tetrahydrofuran (THF, 600 mL) suspension of NaH (15 g, 0.38 mol, 60% dispersed in mineral oil) at 0 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0 °C for 30 min. Subsequently, methyl iodide (67 g, 0.47 mol) was added to the reaction system and the reaction mixture was warmed to 60 °C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble impurities. The filtrate was washed with water and subsequently extracted with ethyl acetate (EtOAc, 3 x 300 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether (PE):ethyl acetate (EtOAc) = 5:1) to afford 1-benzyl-3-methylpiperidin-4-one (30 g, 47% yield) as a yellow oil.1H NMR (400 MHz, DMSO-d6): δ 7.20-7.35 (m, 5H), 3.58 (s, 2H) 2.95-3.02 (m, 2H), 2.48-2.62 (m, 2H), 2.26-2.32 (m, 1H), 2.10-2.18 (m, 1H), 2.00 (q, 1H), 0.81 (d, 3H).

References

[1] Patent: WO2010/114971, 2010, A1. Location in patent: Page/Page column 138
[2] Patent: US5789595, 1998, A
[3] Patent: US4639522, 1987, A
[4] Patent: WO2016/107832, 2016, A1. Location in patent: Page/Page column 90